New York State Route 385 (NY 385) is a state highway in Greene County, New York, in the United States. It runs from the village of Catskill to the village of Coxsackie, serving as an alternate route of U.S. Route 9W between the two locations. While US 9W follows a more inland routing, NY 385 runs along the Hudson River and serves the village of Athens. Modern NY 385 is the original routing of US 9W between Catskill and Coxsackie. NY 385 was originally assigned c. 1932 to what is now US 9W between Catskill and Coxsackie; however, the alignments of both routes were flipped by the following year.

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NY 385 begins at a fork from US 9W (West Bridge Street / Maple Avenue) in the village of Catskill. Proceeding northeast along West Bridge Street, NY 385 is a two-lane mixed residential/commercial street through the southern end of the village, becoming a commercial street just before crossing over Catskill Creek. After Catskill Creek, the route enters downtown Catskill, crossing northeast into another residential neighborhood, where it junctions with Spring Street. At Spring Street, NY 385 turns north while Bridge Street dead-ends two blocks away. NY 385 along Spring Street is primarily residential, passing several blocks of homes through Catskill, soon reaching a junction with NY 23 and access to the Rip Van Winkle Bridge, which crosses the Hudson River.[4]

NY 385 continues north from NY 23, dropping the Spring Street moniker as it enters the town of Catskill. Still a two-lane residential road, the route begins paralleling the CSXWest Shore Line as it enters the hamlet of Hamburg. Northeast of Hamburg, NY 385 continues winding northeast into the town of Athens. Passing several commercial businesses along the way, the route bends eastward towards the Hudson River before turning northeast past a junction with County Route 53 (CR 53 or Howard Hill Road). After CR 53, NY 385 becomes a wooded roadway, soon bending eastward along the riverbanks into the village of Athens, where it gains the Washington Street moniker.[4]

NY 385 north of the village of Athens

The first stretch into the village of Athens is primarily wooded, but as it comes to near the riverbank, NY 385 turns northeast into the developed portion of the community, becoming the main north–south road through the village. NY 385 meets Second Street at the center of the village, changing names to North Washington Street as it turns northward along the riverbank through Athens. Near a junction with River Road, the route drops the North Washington Street moniker as it crosses back into the town of Athens. Remaining a two-lane rural road, NY 385 continues north into the town of Coxsackie. In Coxsackie, NY 385 becomes a two-lane residential street through the town, winding northward through the municipality for several miles. As the Hudson River soon returns towards NY 385, the route turns northwest and enters the village of Coxsackie.[4]

Now in the village, NY 385 gains the Washington Avenue moniker, winding northwest through the village as a two-lane residential street. At the intersection with Sunset Boulevard, the route turns northward, reaching a junction with Mansion Street. At this junction, NY 385 turns northwest on Mansion Street and continues through another residential section of the village. The route passes a merge with Van Dyke Street, where it becomes a more straight route towards the west-northwest. Crossing under the West Shore Line, NY 385 enters downtown Coxsackie, becoming the main street through the village. After a bend to the west, NY 385 reaches a junction with US 9W, the northern terminus of NY 385. At the other side of the junction, NY 81 continues west past US 9W towards Albany County.[4]